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33646839200
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note
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The acylation reaction required using 2 equiv of LiHMDS to complete probably due to the generation of more acidic α-H of 12 than that of N-Boc 11. The addition of excess base was responsible for the racemization of the resulting ester.
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21
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33646854806
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note
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35S-GTPγS functional assay (see Ref. 2a). Compound 2 (30 nM) was used as the agonist.
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22
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2442534745
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Hale J.J., Neway W., Mills S.G., Hajdu R., Keohane C.A., Rosenbach M., Milligan J., Shei G.-J., Chrebet G., Bergstrom J., Card D., Koo G.C., Koprak S.L., Jackson J.J., Rosen H., and Mandala S. Bioorg. Med. Chem. Lett. 14 (2004) 3351
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Rosenbach, M.6
Milligan, J.7
Shei, G.-J.8
Chrebet, G.9
Bergstrom, J.10
Card, D.11
Koo, G.C.12
Koprak, S.L.13
Jackson, J.J.14
Rosen, H.15
Mandala, S.16
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23
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33646852698
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note
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Compounds 22f and 22g were prepared by chiral separation of their corresponding racemic methyl ester on Chiralcel OD 2 × 25 cm column (eluted with EtOH/heptane (v:v = 15:85) at rate of 8.0 mL/min), followed by saponification.
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